90+ Second Date Questions to Deepen Your Connection

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Get a good convo going with these fun, meaningful, and insightful questions

Co-authored by Renee Slansky and Annabelle Reyes

Last Updated: August 25, 2025 Fact Checked

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• Playful Questions
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• Low-Key Personal Questions
|
• Deeper Personal Questions
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• Love & Relationship Questions
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• Questions about Your Connection
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• Expert 2nd Date Advice

|Show more |Show less

So you’ve had an amazing first date, and now it’s time to get to know each other better on your second date. Chances are that you’ve covered the basics already, so your second date is your chance to really delve deeper into your connection and learn more about your compatibility. For this article, we’ve compiled a thorough list of great second date questions to help you do just that, complete with expert insights from professional dating coaches and matchmakers.

2nd Date Questions

According to dating coach Renee Slansky, a second date is when you’re starting to invest more time into the connection. As a result, it’s a good idea to ask slightly deeper questions that will help you get to know this person better and figure out whether there’s potential. For example:

• What music are you super into right now?
• Who in your life would you say you’re closest to?
• What’s the best advice you’ve ever received?
• What qualities do you look for most in a partner?
• Do you have any relationship dealbreakers?
• How did you feel immediately after our first date?

Steps

Section 1 of 6:

Playful & Lighthearted Questions

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1. 
   Get things started with some playful (but insightful!) questions. On a second date, you’ll want to connect on a deeper level than you did on the first date. Still, you don’t want to jump into intense personal questions right off the bat—you’ll need to get the conversation flowing first. Luckily, we’ve compiled a few lighthearted questions that still hint at deeper aspects of their personality, so you can break the ice while also getting to know them better.

   • What song are you totally obsessed with right now?
   • In a movie about your life, what actor would you want to play you?
   • If you were an animal, which one would you be?
   • Do you have any tattoos? And if so, what do they mean?
   • If you could have a superpower, which one would you pick?
   • What was the most memorable vacation you ever went on?
   • If you could only eat one type of food for the rest of your life, what would it be?
   • What movie can you watch over and over again?
   • Which TV show character do you think matches your personality best?
   • Do you like cooking, or do you prefer ordering takeout?
   • If you could have a personal chef or a chauffeur, which would you pick?
   • What does your ideal Saturday night look like?
   • Do you have any hidden talents we didn’t talk about on our last date?
   • What’s your most controversial hot take on a popular musician or actor?
   • What’s been the highlight of your week so far?
   • Have you done anything super cool or interesting since we last hung out?
   • Have you read any good books lately that you’d recommend to me?
   • What type of vibe is your go-to Spotify playlist right now?
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Section 2 of 6:

Safe & Low-Key Personal Questions

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1. 
   Take things to the next level with some slightly more personal questions. Once you’ve gotten the conversation going, you can start to ease into more personal topics. For example, “Ask them about their favorite subject to learn in high school or college,” or “ask them about their favorite place to travel and why,” suggests dating coach Lauren Sanders. These types of questions give you insight into their history and personality, while still steering clear of subjects that are too risky or intense. Here are some more examples:

   • Were you more of a rebel or a rule-follower as a kid?
   • Who was your best friend growing up? Are you still close?
   • Was there a high school or college class that really stuck with you?
   • If you won the lottery tomorrow, what would you do with the money?
   • If you could instantly become an expert at anything, what would you choose?
   • What was your dream job when you were little?
   • If you could go to dinner with anyone, living or dead, who would you pick?
   • Where would you say is your “happy place”?
   • What’s the best book you’ve ever read?
   • What’s your #1 favorite movie of all time?
   • What’s your favorite way to unwind after the work day?
   • Do you have a favorite meal of all time?
   • What’s the best concert you’ve ever been to?
   • If you could go on an unexpected vacation anywhere, where would you pick?
   • Have you tried out any new hobbies lately? Do you like them?
   • What situations make you feel the most awkward?
   • What’s the funniest experience you’ve ever had?
   • Do you have a favorite childhood memory?
   • Did you play sports when you were growing up?
   • Do you like to have things planned out, or do you like to go with the flow?
   • Do you have any funny or quirky little habits?
   • Do you have any silly pet peeves?
   • What’s something you’re genuinely bad at? Like, you’ve tried very hard to learn how to do it, but it just never works out?

Section 3 of 6:

Deeper, More Intense Personal Questions

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1. 
   Intensify your connection with deeper personal questions. If you’re really vibing and hitting it off, it could be time to steer the convo to deeper topics, so you can assess your compatibility. According to Sanders, if you’re compatible with someone, “You’ll share some common interests, values, and life goals,” and “you’ll also share a lot of the same beliefs about life in general, such as religious beliefs.” If you think you could see a future with this person, it’s a good idea to ask about a few of these things to get an idea of where they stand. Here are some examples:

   • What three words do you think your friends and family would use to describe you?
   • Do you think your idea of yourself matches how the people closest to you see you?
   • Do you consider yourself more of an introvert, extrovert, or somewhere in between?
   • Who are the people in your life who are most important to you?
   • Do you have a close relationship with your parents?
   • What qualities do you value most in a friend?
   • If you had to pick your top 3 core values, what would you say they are?
   • When was the last time you surprised yourself?
   • What are you most passionate about?
   • What’s the nicest thing someone’s done for you recently?
   • If your younger self could see you now, what do you think they’d say?
   • When you picture your life in 5 years, what does it look like?
   • What’s your favorite and least favorite thing about your job?
   • What’s one thing you want to learn, or one skill you want to improve?
   • What’s the biggest goal you have your sights set on right now?
   • Which of your achievements are you most proud of?
   • What’s something I’d never guess about you?
   • How important is religion or spirituality to you?
   • What’s a charitable cause or social justice issue you are a lot about?
   • Is there anything about your life you’d really like to change or improve?
   • If you had a paid month off of work, how would you spend it?
   • If you had to pick one person who has changed your life the most, who would it be?
   • What’s the best compliment someone ever gave you? Why do you think it meant so much to you?
   • Is there a moment in your life you’d go back and change if you could? Or do you think everything happens for a reason?
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Section 4 of 6:

Love & Relationship Questions

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1. 
   Amp up the romance with some questions about love. You can learn a lot about a person by their attitude toward love and their relationship history, so it can be super helpful to ask about these things if you’re trying to connect with your date on a deeper level. “Ask them about the first time they fell in love,” suggests Sanders. Or, “ask them about their last breakup, and why it didn’t work out,” or “their worst online dating experience, and how they handled it.” Here are a few more suggestions:

   • When was the first time you fell in love? What was that relationship like?
   • Do you have any silly or funny online dating stories?
   • What are the top 3 most important qualities you’re looking for in a partner?
   • What’s your communication style like in a romantic relationship?
   • When was your last serious relationship?
   • What’s the best dating advice anyone has ever given you?
   • Do you prefer fancy or low-key date nights?
   • How important do you think physical attraction is in relationships?
   • What would you say is the most attractive quality a person can have?
   • Do you have a favorite love song? Or a favorite romantic movie?
   • What does a healthy relationship look like to you?
   • What do you think makes two people truly compatible?
   • Do you have any dealbreakers in dating or relationships?
   • Would you consider yourself a particularly mushy or romantic person?
   • How much do you think people need to have in common to be a good match?
   • Is there something you’d do differently in your last relationship if you could?
   • Do you think you have a specific “type”? Or do you tend to like all sorts of people?
   • What do you think your love language is? Do you have different ones for giving and receiving love?
   • What do you think is the most important lesson you’ve learned from a past relationship?

Section 5 of 6:

Questions about Your Connection

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1. 
   Ask them about your connection to get an idea of where things are going. If you’re having a great second date and really connecting with each other, it’s a good idea to ask them a few questions about how they see you. This is a great way to get some clues about whether or not they see potential for the two of you.

   • What’s the first thing you noticed about me when we met in person?
   • What were you thinking immediately after our first date?
   • Was there anything about me that surprised you?
   • What do you think are the biggest things we have in common?
   • What made you decide that you wanted to go on a second date with me?
   • What drew you to me? (Either in-person or on your dating profile if you met online.)
   • Was your first impression of my dating profile different from your impression of me in person?
   • Is there anything you’ve been wanting to ask me or learn more about since our first date?
   • What types of dates or activities do you think the two of us would really enjoy doing together?
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Section 6 of 6:

Expert Advice for a Great 2nd Date

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1. 
   1
   Explore each topic fully, rather than jumping from subject to subject. If you ask too many rapid-fire questions at once, it may start to feel like a stressful job interview, rather than a romantic date. To combat this, dating coach Lisa Shield tells her clients to dig into each individual topic, rather than skipping around from subject to subject too quickly. “Really great conversation happens when you take one topic and go deeper with it,” she says.

   • For example, you might ask, “Where did you grow up?” And your date may reply, “I grew up in Detroit.”
   • Instead of just saying “cool,” and moving on to the next topic, Shield recommends asking thoughtful follow-up questions to explore your date’s experience growing up more deeply.
   • “You might say, ‘Wow, tell me about Detroit. What was it like growing up there? I heard that Detroit is really having a renaissance right now,’” suggests Shield.
   • This allows the conversation to flow more naturally and get to deeper places, without making it feel too much like an interrogation.
   EXPERT TIP

   

   John Keegan

   Dating Coach

   John Keegan is a Dating Coach and motivational speaker based in New York City. With over 10 years of professional experience, he runs The Awakened Lifestyle, where he uses his expertise in dating, attraction, and social dynamics to help people find love. He teaches and holds dating workshops internationally, from Los Angeles to London and from Rio de Janeiro to Prague. His work has been featured in the New York Times, Humans of New York, and Men's Health.

   

   John Keegan
   Dating Coach

   Try playing a guessing game. For example, you could try to guess where they grew up based on their behavior and mannerisms. This ends up being a lot more fun and engaging than just asking where they’re from, and it helps the conversation flow more freely.
2. 
   2
   Narrow your list down to only a few super deep questions. Although it is a good idea to prepare a few more personal questions for your date, you don’t want to have too many. “When it’s really deep questions, just narrow it down to the most important four or five,” recommends Sanders. Remember, this is still a second date, not a 10th date. You want to learn more about them, but you also want to have fun, and you don’t want the whole conversation to be too heavy or intense.
3. 
   3
   Make sure the conversation is equally balanced. “One of the biggest complaints I get from my coaching clients is [that] the person they went out with went on and on talking about themselves and asked very little [about the other person],” explains dating coach Judith Gottesman, MSW. On a great date, the two of you should be talking about an equal amount, so if you notice that you’re talking a lot more than they are, try to reel it in for a bit and start asking them questions about themselves.

   • Focus on being a good listener while they talk, too. Make eye contact, face them, and nod and react to what they’re saying with your facial expressions.
   • Try not to zone out, and no matter what you do, never scroll through your phone while they’re talking!
4. 
   4
   Ask them if they’d like to go on a third date. If your date is going super well, you might be wondering when to suggest that the two of you meet up again. “I say immediately after the second date would be a good timeline to ask,” suggests Sanders. “Maybe once that person is at home and you’ve checked on them to make sure they’re home safe, tell them when you want to see them again. That’d be the perfect time.”

   • “You don’t want to wait too long after a date to ask them out again because they may think that you’re not interested. So I think it’s always important to make sure that person knows you’re interested by following up with ‘When can I see you again?’” explains Sanders.
   • So, if your second date went great and you see real potential with this person, take a chance and ask if they want to go on a third date sometime soon! Chances are they’re just as excited about the connection as you are.
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